Antimycobacterial activity of novel hydrazide-hydrazone derivatives with 2H-chromene and coumarin scaffold

被引：83

作者：

Angelova, Violina T. ^{[1
]}

Valcheva, Violeta ^{[2
]}

Vassilev, Nikolay G. ^{[3
]}

Buyukliev, Rosen ^{[1
]}

Momekov, Georgi ^{[4
]}

Dimitrov, Ivan ^{[1
]}

Saso, Luciano ^{[5
]}

Djukic, Mirjana ^{[6
]}

Shivachev, Boris ^{[7
]}

机构：

[1] Med Univ Sofia, Dept Chem, Fac Pharm, 2 Dunav St, Sofia 1000, Bulgaria

[2] Bulgarian Acad Sci, Inst Microbiol, 26 Acad G Bonchev St, BU-1113 Sofia, Bulgaria

[3] Bulgarian Acad Sci, Ctr Phytochem, Inst Organ Chem, Lab Nucl Magnet Resonance, 9 Acad G Bonchev St, BU-1113 Sofia, Bulgaria

[4] Med Univ Sofia, Lab Expt Chemotherapy, Dept Pharmacol Pharmacotherapy & Toxicol, Fac Pharm, 2 Dunav St, Sofia 1000, Bulgaria

[5] Sapienza Univ, Dept Physiol & Pharmacol Vittorio Erspamer, Ple Aldo Moro 5, I-00185 Rome, Italy

[6] Univ Belgrade, Dept Toxicol, Fac Pharm, 450 Vojvode Stepe St, Belgrade 11221, Serbia

[7] Bulgarian Acad Sci, Inst Mineral & Crystallog, 107 Acad G Bonchev St, Sofia 1113, Bulgaria

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 02期

关键词：

Antitmycobacterial activity; 2H-Chromene; Coumarin; Cytotoxicity; Hydrazide-hydrazone; ANTITUBERCULAR ACTIVITY; ISONIAZID DERIVATIVES; TUBERCULOSIS; DESIGN; AGENTS; TB; MDR;

D O I：

10.1016/j.bmcl.2016.11.071

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

This study reports the synthesis of new 2H-chromene or coumarin based acylhydrazones, which were evaluated for their in vitro antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and compared to the first-line antituberculosis drugs, isoniazid (INH) and ethambutol (EMB). The most active compounds 7m (MIC 0.13 mu M), 7o (MIC 0.15 mu M) and 7k (MIC 0.17 mu M) demonstrated antimycobacterial activity at submicromolar concentration level and remarkably minimal associated cytotoxicity in the human embryonic kidney cell line HEK-293T. Structure-activity relationship for this class of compounds has been established. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：223 / 227

页数：5

共 34 条

[1] A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial [J].

Alvey, Luke ;

Prado, Soizic ;

Huteau, Valerie ;

Saint-Joanis, Brigitte ;

Michel, Sylvie ;

Koch, Michel ;

Cole, Stewart T. ;

Tillequin, Francois ;

Janin, Yves L. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (17) :8264-8272

[2] Diversity-oriented synthesis of furo[3,2-f]chromanes with antimycobacterial activity [J].

Alvey, Luke ;

Prado, Soizic ;

Saint-Joanis, Brigitte ;

Michel, Sylvie ;

Koch, Michel ;

Cole, Stewart I. ;

Tillequin, Francois ;

Janin, Yves L. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (06) :2497-2505

[3] Antiproliferative and antioxidative effects of novel hydrazone derivatives bearing coumarin and chromene moiety [J].

Angelova, Violina T. ;

Vassilev, Nikolay G. ;

Nikolova-Mladenova, Boryana ;

Vitas, Jasmina ;

Malbasa, Radomir ;

Momekov, Georgi ;

Djukic, Mirjana ;

Saso, Luciano .

MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (09) :2082-2092

[4] 2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents [J].

Azizmohammadi, Mohammad ;

Khoobi, Mehdi ;

Ramazani, Ali ;

Emami, Saeed ;

Zarrin, Abdolhossein ;

Firuzi, Omidreza ;

Miri, Ramin ;

Shafiee, Abbas .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 59 :15-22

[5] Antitubercular Drug Development: Current Status and Research Strategies [J].

Barot, Kuldipsinh P. ;

Nikolova, Stoyanka ;

Ivanov, Illiyan ;

Ghate, Manjunath D. .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2013, 13 (11) :1664-1684

[6] Synthesis, structure-activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents [J].

Basanagouda, Mahantesha ;

Jambagi, Vishwanath B. ;

Barigidad, Nivedita N. ;

Laxmeshwar, Sandeep S. ;

Devaru, Venkatesh ;

Narayanachar .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 74 :225-233

[7]

Bijev A., 2010, J. Uni. Chem. Tech. Metal, V45, P111

[8]

CANETTI G, 1969, B WORLD HEALTH ORGAN, V41, P21

[9] Antitubercular Activity of New Coumarins [J].

Cardoso, Silvia H. ;

Barreto, Milena B. ;

Lourenco, Maria C. S. ;

Henriques, Maria das Gracas M. de O. ;

Candea, Andre L. P. ;

Kaiser, Carlos R. ;

de Souza, Marcus V. N. .

CHEMICAL BIOLOGY & DRUG DESIGN, 2011, 77 (06) :489-493

[10] A Web-Based Platform for Designing Vaccines against Existing and Emerging Strains of Mycobacterium tuberculosis [J].

Dhanda, Sandeep Kumar ;

Vir, Pooja ;

Singla, Deepak ;

Gupta, Sudheer ;

Kumar, Shailesh ;

Raghava, Gajendra P. S. .

PLOS ONE, 2016, 11 (04)

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